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Ammonium formate → HCID 59375151, Verbindung

HRID 662003
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 662003
[CH3:1][C:2]1[C:3](=[O:35])[N:4]([C:8]2[C:9]([CH3:34])=[C:10]([C:14]3[C:26]4[C:25]5[C:20](=[CH:21][C:22]([C:27]([OH:30])([CH3:29])[CH3:28])=[CH:23][CH:24]=5)[NH:19][C:18]=4[C:17]([C:31]([NH2:33])=[O:32])=[CH:16][CH:15]=3)[CH:11]=[CH:12][CH:13]=2)[CH2:5][C:6]=1[CH3:7].C([O-])=O.[NH4+]>CO.[Pd].C(Cl)Cl>[CH3:1][CH:2]1[CH:6]([CH3:7])[CH2:5][N:4]([C:8]2[C:9]([CH3:34])=[C:10]([C:14]3[C:26]4[C:25]5[C:20](=[CH:21][C:22]([C:27]([OH:30])([CH3:29])[CH3:28])=[CH:23][CH:24]=5)[NH:19][C:18]=4[C:17]([C:31]([NH2:33])=[O:32])=[CH:16][CH:15]=3)[CH:11]=[CH:12][CH:13]=2)[C:3]1=[O:35]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 2

HCID 2723923Ammonium formate4×HCID 66606416HCID 66606416, Verbindung

Produkt 1

HCID 59375151HCID 59375151, VerbindungAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysator2×HCID 887MethanolLösungsmittel
HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

A mixture of 4-(3-(3,4-dimethyl-2-oxo-2,5-dihydro-1H-pyrrol-1-yl)-2-methylphenyl)-7-(2-hydroxypropan-2-yl)-9H-carbazole-1-carboxamide (Example 81-21, 20 mg, 0.043 mmol) and ammonium formate (27.0 mg, 0.428 mmol) in methanol (5 mL) was treated with 10% palladium on charcoal (20 mg, 0.019 mmol). The mixture was stirred under nitrogen at rt for 2 h. Additional ammonium formate (27.0 mg, 0.428 mmol) was added and the mixture was stirred at rt overnight. More ammonium formate (57 mg) and 10% palladium on charcoal (40 mg) were added, and after 6 h more additional ammonium formate (57 mg) was added. The mixture was again stirred overnight, then was diluted with DCM and filtered through Celite. The filtrate was washed with water, dried and concentrated. The residue was purified by preparative HPLC and the appropriate effluent fractions were made basic with 1 M aqueous sodium hydroxide and extracted twice with DCM. The combined organic phases were washed with water, dried and concentrated to provide 4-(3-(3,4-dimethyl-2-oxopyrrolidin-1-yl)-2-methylphenyl)-7-(2-hydroxypropan-2-yl)-9H-carbazole-1-carboxamide as a white solid (11 mg, 55%), which was a mixture of diastereomers. Mass spectrum m/z 452.1 (M+H—H2O)+.

Aufarbeitung

  1. stirringthe mixture was stirred at rt overnight
  2. waitThe mixture was again stirred overnight
  3. filtrationfiltered through Celite
  4. washThe filtrate was washed with water
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by preparative HPLC
  8. extractionextracted twice with DCM
  9. washThe combined organic phases were washed with water
  10. customdried
  11. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c64b8144d1c946b2af4bff75304053f0
Quelldatensatz
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08084620B2

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